This invention is a structural member and, in particular, is a structural member that was developed for use as a floor for a refrigerated or other truck or trailer, but can also be used as a roof for homes and commercial buildings, as floating and other docks and dock covers, as cross arms for utility poles, as steps, as walks and walkways, as seawalls, as fence posts, as patio decks, as building foundations, as beams, as structural panels, as windows, as piers, as outdoor furniture, as horse trailers, and as stalls and barnyard structures.
In another aspect, the invention is an intermediate composition that is admirably suited for use in producing the structural member described above, a Dyligomer, as defined below, which is used in formulating the foregoing intermediate composition, and a cured material that can be produced by subjecting the intermediate composition sequentially to condensation polymerization with an isocyanate and then to addition polymerization.
In still another aspect the invention is a wall panel and a block both of which can be used in constructing buildings.
Refrigerated trucks and trailers usually have aluminum floors made up of a number of extruded sections, each of which has a plurality of parallel, longitudinally-extending channels. Adjacent ones of the channels have common sidewalls, and webs which are parallel to one another and are structurally integral with opposite edges of the sidewalls. The sections are welded together to make an entire floor, which may have inside dimensions as great as 102 inches (2.6 meters) by 52xc2xd feet (16 meters). The aluminum floor must be insulated from the metal of the truck or trailer by which it is supported. This is usually accomplished by attaching spaced transverse wooden members to the supporting metal of the truck or trailer, and attaching the aluminum floor to the wooden members. After the assembly is complete, a froth foam is injected from a wand into the spaces which are below the floor and between the wooden members, where the floor is unsupported. Such floors leak, and must be replaced frequently, to a large extent because movement of a trailer or truck while in operation on a highway often exerts enormous forces tending to strip screws that are supposed to hold the floor to the trailer or truck and, as a consequence, stripping frequently occurs after a short time of service. Wet floors are particularly subject to this stripping.
Isocyanates and compositions that are polymerizable by condensation of the NCO groups of isocyanates with compounds having active hydrogens have been used widely since World War II to produce a broad spectrum of products ranging from coating compositions to medical appliances.
The instant invention is based upon the discovery of a structural member made up of the aluminum floor described above, or another floor that is similar in design, but made of thinner aluminum or of another metal, and a cellular material having urethane groups in its molecular structure and an apparent density of at least 8 pounds per cubic foot (0.13 gm per cm3) bonded to the aluminum because of chemical affinity between the aluminum and the foam. As is subsequently explained in more detail, it is also desirable to compound the urethane to promote adhesion. As a consequence of its being in intimate contact with and bonded to the aluminum floor, the urethane foam supports the floor throughout its entire surface. Preferably, the structure also includes, as a substrate, a sheet of a second material, such as expanded polystyrene, plywood or the like, to which the urethane foam is also bonded because of the chemical affinity between the foam and the substrate. Most desirably, the second sheet is also the aluminum floor described above, with its parallel channels extending in a different direction than do the channels in the first floor, e.g., at right angles to the channels of the first floor. The structural member according to the invention has been found to be water tight and to have strength properties which indicate that it should have substantially extended service life by comparison with the previously described floor. The structural member can also be produced from sheet materials having the same shape as the aluminum floor, but made of metals other than aluminum, and can have various shapes other than that of the floor.
In another aspect, the instant invention is based upon the discovery of certain compounds, subsequently herein xe2x80x9cDyligomersxe2x80x9d, which can serve as monomers in a polycondensation reaction with a polyisocyanate and can also serve as monomers in an addition propagation reaction with an unsaturated cross lining monomer. These Dyligomers can be produced from diisocyanates, the triglyceride of ricinoleic acid, and such compounds as 1,3-propanediol, 1,4-butanediol and 1,4-but-2-enediol; they can be mixed with other compounds which have active hydrogens, are ethylenically unsaturated, or both, and fillers, catalysts, water and the like, and the mixtures can be condensed to a thermoset condition with the same diisocyanate used to produce the Dyligomer, with another diisocyanate, or with a polyisocyanate. The thermoset condensate then cures further by addition polymerization involving the ethylenic unsaturation of the ricinoleic acid triglyceride or other ethylenically unsaturated compound moiety of the Dyligomer, or both. The triglyceride of ricinoleic acid, which is the principal constituent of castor oil, is an example of a compound which is capable of serving as a monomer in a polycondensation reaction with a diisocyanate and is also capable of serving as a monomer in an addition propagation reaction with an unsaturated cross linking monomer, having three hydroxyl groups which are at least potentially capable of a polycondensation reaction with a polyisocyanate and three ethylenic 
double bonds which are at least potentially capable of an addition propagation reaction with an unsaturated crosslinking monomer.
Other examples of compounds which are capable of undergoing both types of reaction include 1,2,3-trihydroxy propene, with three hydroxyl groups and one ethylenic double 
bond, 1,3-propene diol with two hydroxyl groups and one ethylenic double bond, and 1,4-but-2-ene diol, with two hydroxyl groups and one ethylenic double bond.
While these and other compounds can serve as monomers in a poly-condensation reaction with a polyisocyanate and can also serve as monomers in an addition propagation reaction with an unsaturated cross linking monomer, their use in practicing the instant invention is only as starting materials in producing Dyligomers, which can also serve as monomers in both polycondensation reactions and in addition propagation reactions. An example of such a Dyligomer, which can be produced by reaction of one molecule of the triglyceride of ricinoleic acid and one molecule of 1,4-but-2-ene diol with one molecule of 2,4-toluene diisocyanate (xe2x80x9cTDIxe2x80x9d), has the following structure, and is hereinafter called xe2x80x9cDyligomer Ixe2x80x9d: 
Dyligomer I has four ethylenic double bonds and three hydroxyl groups; it can be stored for extended periods of time.
U.S. Pat. No. 2,787,601, granted Apr. 2, 1957 to Detrick et al., discloses the production of a cellular plastic material by reaction of an arylene diisocyanate with a fatty acid triglyceride, citing xe2x80x9cGerman Plastics Practice,xe2x80x9d De Bell, Goggin and Gloor, 1946, pp. 316 and 463-465 as authority for the statement (column 1, second paragraph of the patent):
xe2x80x9cCellular plastic products or plastic foams have been prepared in which isocyanates are used as one of the reactants * * *. In these products the cellular materials are prepared from alkyd resins which contain free carboxy groups.xe2x80x9d
The patent says that its cellular plastic product is prepared in two steps, a first in which a prepolymer is made by reacting a fatty acid triglyceride containing hydroxy groups with enough of a diisocyanate that, when not more than 47.5% of the total isocyanate groups in the diisocyanate have reacted with the hydroxy groups on the fatty acid radicals, there are no longer any remaining hydroxyl groups, and a second step in which the prepolymer is reacted with water and a tertiary amine catalyst. Upon addition of the water and the tertiary amine catalyst, the patent says, the reaction mass immediately begins to foam due to the reaction of the unreacted isocyanate groups with water to form CO2 and substituted ureas. The following structure can be postulated, it is said, for the prepolymer produced by reaction of the triglyceride of ricinoleic acid with 2,4-TDI: 
U.S. Pat. No. 5,306,798 discloses a xe2x80x9cpolyurethane embedding compositionxe2x80x9d suitable for use in a dialyzer, and produced from an A Component containing a large proportion of castor oil and a modified diphenylmethane diisocyanate (xe2x80x9cMDIxe2x80x9d) B Component. One example of a Component A is composed of 5 parts by weight of a polyether-polyol, 94.95 parts by weight of castor oil and 0.05 part by weight of a catalyst composed of di-n-octyltin bis(2-ethylhexyl thioglycolate) and mono-n-octyltin tris(2-ethylhexyl thioglycolate). The patent discloses the preparation of the modified MDI B component (NCO content of 23 percent by weight) by reacting 4,4xe2x80x2-MDI with a mixture of dipropylene glycol and a polyoxypropylene glycol having a hydroxyl number of 250.
U.S. Pat. No. 5,290,632 discloses a Component A of a two component formulation as comprising castor oil and a low molecular weight polyol while component B is a polymeric MDI. An elastomer is an alternative constituent of component A. Examples of polymeric MDI""s are said to be available from Dow Chemical under the registered trademark PAPPI 2027 (average molecular weight 340-380, average functionality 2.6-2.7) and under the designation xe2x80x9cMondur XP-744xe2x80x9d.
U.S. Pat. No. 5,278,223 is concerned with the polyol component of a urethane formulation, which is required to include (1) branched chain polyols with ester and ether groups, (2) glycerol esters, e.g., castor oil and (3) low viscosity monofunctional alcohols of oleophilic character. The reaction of such a polyol constituent with technical methylene diphenyldiisocyanate xe2x80x9cMDIxe2x80x9d, TDI or the like is disclosed.
U.S. Pat. No. 5,166,301 discloses a prepolymer made from methane dicyclohexyl diisocyanate, a polyoxypropylene ether polyol, methane-dicyclohexyl diisocyanate and a silane, and reaction of the prepolymer with a component composed mainly of polyoxypropylene ether polyol and diethyltoluene diamine plus minor amounts of m-xylene diamine, organo-bismuth and water. Castor oil is named as a xe2x80x9chydroxy functional moietyxe2x80x9d.
U.S. Pat. No. 5,157,101 discloses the reaction of liquid polyisocyanate from Mobay (xe2x80x9cMondur PFxe2x80x9d, 26.6 weight percent NCO) with polybutadiene polyols and amines.
U.S. Pat. No. 5,155,165 discloses the reaction of isocyanates or an isocyanate terminated prepolymer with polyhydroxy compounds, which are broadly defined, by a process which produces xe2x80x9cpolyurethane polyurea particlesxe2x80x9d which can be, but are not necessarily, pigmented.
U.S. Pat. No. 5,061,776 discloses a thermal transfer adhesive composed of 30 to 70 weight percent of an aliphatic diisocyanate or triisocyanate prepolymer, 5 to 15 weight percent of a polyether diol or triol, 20 to 40 weight percent of castor oil, 5 to 20 weight percent of an epoxy resin containing 2 or more hydroxyl groups and 0.006 to 0.008 weight percent of a catalyst for the reaction of isocyanate groups with hydroxyl groups. Dibutyl tin dilaurate is said to be the preferred catalyst.
U.S. Pat. No. 4,990,586 discloses the production of a polyurethane by reaction between a polyisocyanate and a polyol in the presence of a diphenyl methane diamine with one amine group and either one or two alkyl group substituents on each phenyl. The preferred polyol is said to be castor oil.
U.S. Pat. No. 5,021,535 discloses an abrasion resistant urethane composition for automobile undercoating made from unmodified castor oil and MDI-alkylene oxide prepolymers. The castor oil can be modified by an addition of a cyclohexanone-formaldehyde condensate and can be further modified by an addition of a neopentyl glycol adipic acid reaction product.
U.S. Pat. No. 4,990,586 discloses the production of a polyurethane by reaction between a polyisocyanate and a polyol in the presence of a diphenyl methane diamine with one amine group and either one or two alkyl group substituents on each phenyl. The preferred polyol is said to be castor oil.
U.S. Pat. No. 4,987,204 discloses a coating composition xe2x80x9ccomprising 2-100 parts by weight of fluororesin, 5-100 parts by weight of a silicone oil, and a solvent to 100 parts of a urethane prepolymer * * * comprising a polyol, castor oil polyol, and a polyisocyanate * * *.xe2x80x9d
U.S. Pat. No. 4,968,725 discloses a dental adhesive which includes a urethane prepolymer produced by reacting an isocyanate with a polyol (castor oil is named as an example), a xe2x80x9cradical-polymerizable unsaturated monomer and a photopolymerization initiator, and can also include a polymerizable phosphoric ester.
U.S. Pat. No. 4,877,829 discloses a xe2x80x9cnovel polyurethane resinxe2x80x9d for application to exterior surfaces, including concrete roadways, produced from two components, Component A being composed of ricinoleic triglyceride (conveniently as castor oil) and a low molecular weight polyol (e.g., glycerol) and Component B being composed of either a mixture of MDI isomers or a mixture of MDI with a prepolymer made by reacting MDI with an alkylene oxide. An elastomer is an optional ingredient of the first component. A Table indicates the following ranges of ingredients in parts by weight to be workable: Castor oil 90 to 140, low molecular weight polyol 2 to 10 and Modified MDI 50 to 110. Up to 120 parts of an elastomer and up to 50 parts of molecular sieves can be used in the non-MDI Component A.
U.S. Pat. No. 4,877,455 discloses the autoclaving of castor oil with dicyclopentadiene and hydroxyethyl methacrylate. A maximum temperature of 265xc2x0 C. and a maximum pressure of 80 psi are reported. The product, which is called a graft polyol, when reacted with polymeric MDI (NCO/OH 1.05), produced a urethane said to be considerably more resistant to certain solvents by comparison with urethanes produced from the unmodified castor oil.
U.S. Pat. No. 4,859,735 discloses xe2x80x9cNovel polyurethane formulations especially useful as membranes of the protection of bridge deckings. The polyurethane is prepared by mixing two components, A and B. Component A comprises castor oil modified with a ketone-formaldehyde condensate and also preferably contains an elastomer. Component B is a modified MDI, being a mixture of diphenylmethane diisocyanate and its reaction product with a low molecular weight poly(oxyalkylene).
U.S. Pat. No. 4,789,705 discloses a resin composition comprising a polyisocyanate having an isocyanurate ring obtained by reacting at least one diisocyanate (alkylene, cycloalkylene or aralkylene) with a diol having 10 to 40 carbon atoms or with a polyester polyol (hydrogenated castor oil is said to be xe2x80x9cwithin the scope of the polyester polyol) containing 12-hydroxystearic acid as an essential component in the presence of an isocyanuration catalyst and a nonpolar organic solvent.
U.S. Pat. No. 4,742,087 discloses a prepolymer which contains an excess of an isocyanate component having an average of 2 to 4 NCO groups and a polyol component comprised of an oleochemical polyol prepared by epoxidation of an olefinically unsaturated triglyceride such as castor oil and ring opening with an alcohol.
U.S. Pat. No. 4,677,157 discloses a part A composed, in weight percent, of 62.0 4,4xe2x80x2diphenylnethane diisocyanate, 15.0 polyether polyol, 18.0 castor oil, 1.0 carbon black, 3.0 fumed silica and 1.0 organic thixatrope and mixing part A with an equal volume of Part B composed of 30.0 polyether polyol, 25.0 N,N,N,N-tetrakis(2-hydroxypropyl) ethylene diamine and 45.0 fillers.
U.S. Pat. No. 4,659,748 discloses urethane formulations for repairing cementitious roadways. Excess NCO groups react with moisture that is naturally present. Castor oil and glyceryl trihydroxy oleate are named as examples of organic compounds which react with polyisocyanates. Dibutyl tin dilaurate is named as a catalyst.
U.S. Pat. No. 4,640,801 discloses the autoclaving of castor oil with dicyclopentadiene and hydroxyethyl methacrylate. A maximum temperature of 265xc2x0 C. and a maximum pressure of 80 psi are reported. The product, which is called a graft polyol, when reacted with polymeric MDI (NCO/OH 1.05), produced a urethane said to be considerably more resistant to certain solvents by comparison with urethanes produced from the unmodified castor oil.
U.S. Pat. No. 4,603,188 discloses a urethane composition which has a polyhydroxyl component and a polyisocyanate component. The polyhydroxyl component is made up of 80 to 10 percent by weight of an interesterification product of castor oil and a substantially non-hydroxyl-containing naturally occurring triglyceride oil and 20 to 90 percent by weight of a polybutadiene based polyol. The interesterification product can also contain a low molecular weight polyol.
U.S. Pat. No. 4,598,136 discloses aliphatic embedding masses prepared by preparing a prepolymer having NCO groups by reacting at least one aliphatic diisocyanate with castor oil or a mixture of castor oil with other hydroxyl compounds, e.g., trimethylol propane, and reacting the prepolymer with a mixture containing castor oil, trimethylol propane and N-methyldiethanol amine.
U.S. Pat. No. 4,582,891 discloses a urethane coating composition. The urethane is produced from a polyol component composed of xe2x80x9ca castor oil polyol alone or a mixture of a castor oil polyol and a low molecular weight polyolxe2x80x9d and a polyisocyanate component. The xe2x80x9ccastor oil polyolxe2x80x9d can be castor oil, an interesterification product of castor oil and ethylene oxide or the like, an esterification product of ricinoleic acid and an ethylene oxide or the like adduct of dipropylene oxide or the like. TDI and MDI are named as isocyanates. Dibutyl tin dilaurate is disclosed as a component of a polyol composition, along with castor oil.
U.S. Pat. No. 4,555,536 discloses a polyurethane coating composition produced from (1) a polyol mixture of castor oil or a polyol derived from castor oil and an amine polyol produced by addition reaction of an alkylene oxide with ammonia, an aliphatic amine or the like, and (2) a polyisocyanate compound.
U.S. Pat. No. 4,551,517 relates to a two-component polyurethane adhesive produced by mixing an isocyanate having a functionality of from 2 to 10 with a liquid mixture of anhydrous polyols having more than 10 carbon atoms and 2 or more hydroxyl groups, obtained by reacting (1) epoxidized higher fatty alcohols, (2) epoxidized higher fatty acid esters or (3) epoxidized higher fatty acid amides with aliphatic or aromatic alcohols having a functionality of 1 to 10, with difunctional or trifunctional phenols, or with both, with opening of the epoxide ring. Transesterification of the fatty acid esters, subsequent reaction with C2 to C4 epoxides, or both, is also disclosed. In two examples, the polyols are produced by ring opening epoxidized soy bean oil with methanol. Comparative examples are said to show the superiority of the adhesive of the invention over urethanes made from castor oil.
U.S. Pat. No. 4,433,128 is directed to an embedding mass composed of a polyurethane obtained through reaction of an aromatic polyisocyanate with a mixture of castor oil and trimethylolpropane xe2x80x9cpre-adductxe2x80x9d and a polypropyleneglycol or a mixture of a polypropyleneglycol and trimethylpropane in the presence of a catalyst which is a mixture of a dialkyl tin dicarboxylate and an aliphatic mono- or di-amine. The patent discloses the production of a Component A having an isocyanate content of 18.85 percent from a liquid polyisocyanate based upon MDI, castor oil and trimethylolpropane, the production of a Component B from polypropylene glycol, trimethylolpropane, dibutyl tin dilaurate and 1,4-diasabicyclo(2,2,2)-octane, and the mixing of the two components to produce casting resins. Several German patent applications are acknowledged as prior art, including DE-OS 28 13 197, which is said to disclose the production of xe2x80x9cpolyurethanesxe2x80x9d by reacting an aromatic polyisocyanate with a mixture of castor oil and trimethylol propane to produce a pre-adduct, and polymerizing the pre-adduct with castor oil or a mixture of castor oil with trimethylol propane.
U.S. Pat. No. 4,391,964 is directed to a potting medium composed of a polyurethane obtained through reaction of a polyisocyanate with a mixture of castor oil and trimethylolpropane xe2x80x9cpre-adductxe2x80x9d and reaction of the prepolymer with castor oil or a mixture of castor oil with trimethylolpropane for cross lining. A titanium alkylate, e.g., titanium tetrabutylate, is used as a catalyst.
U.S. Pat. No. 4,378,441 discloses resinous products produced by reacting (A) an alkali metal silicate, (B) an organic monohydroxy compound having a substituent which will split off during the reaction, and (C) a polycarboxylic acid and/or a polycarboxylic acid anhydride. Castor oil can be substituted for a small portion of the polycarboxylic acid.
U.S. Pat. No. 4,375,521 discloses a vegetable oil extended polyurethane produced by reacting an isocyanate terminated polyisocyanate with a polyol (which can be castor oil) in the presence of a vegetable oil such as soybean, safflower, corn, sunflower, linseed, oiticica, coconut, cottonseed, peritta, palm, olive, rape or peanut.
U.S. Pat. No. 4,371,683 discloses that castor oil can be substituted for up to 85 percent of the polyol in an adhesive composed of the reaction product of a novolac, an oxirane and a polyisocyanate.
U.S. Pat. No. 4,344,873 is directed to a potting medium composed of a polyurethane obtained through reaction of a polyisocyanate with a mixture of castor oil and trimethylolpropane xe2x80x9cpre-adductxe2x80x9d and reaction of the prepolymer with castor oil or a mixture of castor oil with trimethylolpropane for cross ling. A dialkyl tin compound is used as a catalyst.
U.S. Pat. No. 4,170,559 discloses the production of a prepolymer (NCO content about 16.2 percent) from 204 g polyoxypropylene glycol (M.W. 400), 205 g castor oil and 795 g MDI, and cure of such a prepolymer with an ester of a polyhydric alcohol having 2 or three OH groups and an aliphatic acid having at least 12 carbons atoms and at least one OH group or epoxy group. The following U.S. patents are cited as disclosing the preparation of prepolymers: U.S. Pat. Nos. 2,625,531; 2,625,532; 2,625,535; 2,692,873; and 2,702,797.
Dyligomer I, above, and other related dyligomers are disclosed in his U.S. Pat. No. 6,284,841, supra, but the present inventor is not aware of any prior art disclosing Dyligomer I or an equivalent thereof, i.e., a compound that has no NCO groups, and is composed of a chemical moiety that is derived from a diisocyanate, and is bonded through urethane groups to two additional chemical moieties which have a plurality of active hydrogens and a plurality of ethylenic double bonds so that they are capable of reacting with an isocyanate to form urethane linkages and, as a consequence, a three-dimensional cross linked polymer, and subsequently and independently, with a cross linking monomer in an addition propagation reaction. Accordingly, he is not aware of prior art disclosing an intermediate composition comprising such a Dyligomer and a cross linking monomer that is sufficiently fluid that fillers it may contain are wet effectively. Finally, he is not aware of prior art disclosing a material that will cure to a thermoset condition which is produced by mixing an isocyanate with such an intermediate composition comprising Dyligomer I or an equivalent and a cross liking monomer.
Accordingly, it is an object of the invention to provide a dyligomer which can serve sequentially as a monomer in a polycondensation reaction with a polyisocyanate and then as a monomer in an addition propagation reaction with an unsaturated cross liking monomer, because it has both ethylenic groups and active hydrogens in its molecule. The dyligomer, as is subsequently explained in more detail, is composed of three chemical moieties, one of which is a moiety derived from a diisocyanate and is bonded to a first of the other moieties through a urethane group and to the second of the other moieties through a different urethane group.
It is another object to provide an intermediate composition composed of a dyligomer, a cross linking monomer reactive by addition polymerization with the double bonds of the dyligomer, a catalyst for the reaction of the dyligomer with an isocyanate to form a urethane, and a free radical catalyst for the addition polymerization of the cross linker.
It is a further object to provide a thermoset material produced by condensing the intermediate composition with the diisocyanate used to produce the dyligomer, with another diisocyanate, or with an isocyanate having more than two NCO groups per molecule.
It is yet another object of the invention to provide a thermoset condensate that has been cured further, after polycondensation, by an addition polymerization reaction involving the ethylenic unsaturation of the dyligomer.
It is still another object to provide a structural member.
It is yet another object to provide a structural panel that is admirably suited for use as a floor in refrigerated trucks and trailers, and in roofs, sidewalls and load bearing walls for homes and commercial buildings.
It is still another object to provide structural members that are admirably suited for use as floating and other docks and dock covers, as cross arms for utility poles, as steps, as walks and walkways, as seawalls, as fence posts, as patio decks, as building foundations, as beams, as structural panels, as piers, as windows, as outdoor furniture, as horse trailers, and as stalls and barnyard structures.
It is yet another object to provide a block which is admirably suited for use in sidewalls and load bearing walls for homes and commercial buildings.
In one aspect, the instant invention is based upon the discoveries that a dyligomer that is stable for extended periods of time can be produced by reacting one molecule of a diisocyanate with two molecules, which can be the same or different, of a compound which has active hydrogens in its structure, and at least one of which has an ethylenic double bond, that the Dyligomer can be mixed with various additives, e.g., a copolymerizable monomer, an inorganic or organic filler, and a free radical catalyst, to produce an intermediate composition that is stable for an extended period of time, and can be mixed with an appropriate amount of a diisocyanate or polyisocyanate to produce a material in which the Dyligomer serves sequentially as a monomer in a polycondensation reaction with the diisocyanate or polyisocyanate and then as a monomer in an addition propagation reaction with the copolymerizable monomer. This material, prior to cure, can be introduced into suitable molds to produce various articles of manufacture, e.g., the previously mentioned structural member that was developed for use as a floor for a refrigerated or other truck or trailer, but can also be used as a roof for homes and commercial buildings, as floating and other docks and dock covers, as cross arms for utility poles, as steps, as walks and walkways, as seawalls, as fence posts, as patio decks, as building foundations, as beams, as structural panels, as windows, as piers, as outdoor furniture, as horse trailers, and as stalls and barnyard structures.
Dyligomer I, as previously explained, can be produced by reacting one molecule of ricinoleic acid triglyceride with one molecule of 2,4-TDI, and one molecule of 1,4-but-2-ene diol. Dyligomer II, which has the following structure, is produced when one molecule of ricinoleic acid triglyceride reacts with one molecule of 2,4-TDI, and one molecule of glycerol: 
Similarly, one molecule of ricinoleic triglyceride can react with one molecule of 2,4-TDI, and one molecule of 1,4-butane diol to produce a dyligomer (hereafter Dyligomer III) having the following structure: 
Other dyligomers that can be produced by reacting one molecule of 2,4-TDI with two molecules of at least one other compound having an active hydrogen are identified in the following table:
The structures of the dyligomers identified in the foregoing table are presented below: 
It will be appreciated that Dyligomers I through V can all be represented by the following formula, where R is alkyl, hydroxy alkyl, dihydroxy alkyl, or hydroxy alkenyl: 
It will also be appreciated that, more generally, the foregoing dyligomers can be represented by the formula 
where B is a chemical moiety formed by reactions involving the NCO groups of a diisocyanate having the formula,
OCNxe2x80x94Bxe2x80x94NCO
and the active hydrogens of OH groups of compounds having the formulas
Axe2x80x94OH and Dxe2x80x94OH
and A and D are chemical moieties formed by the reactions which formed B, and wherein A and D include, in their structures at least two active hydrogens which are parts of OH groups and at least one ethylenic double bond. In addition, it will be appreciated that the properties of the diligomer represented by Formula I depend upon the identity of R. For example, Dyligomer IV has two OH groups and three ethylenic double bonds available for condensation polymerization with an isocyanate and for addition polymerization respectively. However, the geometry of the molecule does not favor either type of reaction. Dyligomer I, on the other hand, has an additional ethylenic double bond and an additional OH group, and the geometry of the molecule favors reaction of both of the additional groups. As might be expected, available evidence indicates that Dyligomer I, by comparison with Dyligomer IV, is capable of a higher degree of condensation polymerization with an isocyanate and of a higher degree of addition polymerization with a cross-linking molecule. Similarly, Dyligomer II and Dyligomer III appear to be capable of a higher degree of condensation polymerization with an isocyanate.
Dyligomers can also be produced from:
(A) other diisocyanates, the triglyceride of ricinoleic acid, and n-butanol, 1,4-butane diol, glycerol, 1,2,3-trihydroxy propene, and 1,4-but-2-ene diol,
(B) diisocyanates, the triglyceride of ricinoleic acid and various polyesters and polyethers having free alcoholic OH groups (such polyesters and polyethers are commercially available, and are sold for use in producing urethanes), and
(C) diisocyanates, n-butanol, 1,4-butane diol, glycerol, 1,4-but-2-ene diol, 1,2,3-trihydroxy propene, various polyesters and polyethers having free alcoholic OH groups (such polyesters and polyethers are commercially available, and are sold for use in producing urethanes) and equivalents for the triglyceride of ricinoleic acid.
Examples of compounds which can be used as equivalents for the ricinoleic acid triglyceride in producing dyligomers include ricinoleic and other fatty acid monoglycerides, ricinoleic and other fatty acid diglycerides and fatty acid esters of various polyesters and polyethers having free alcoholic OH groups, for example, ones which are commercially available for reaction with isocyanates to produce urethanes; and fatty acid monoesters of glycols, and of fatty acid esters which have at least one free alcoholic OH group, and are formed by esterification of alcoholic OH groups of various polyesters and polyethers with fatty acids.
In theory, it is possible to produce dyligomers from diisocyanates, n-butanol, 1,4-butane diol, glycerol, 1,4-but-2-ene diol, various polyesters and polyethers having free alcoholic OH groups (such polyesters and polyethers are commercially available, and are sold for use in producing urethanes) and fatty acids. As a practical matter, however, it is necessary to control the rates of reaction between the diisocyanate and the fatty acid, and between the diisocyanate and the n-butanol or the like so that dyligomers composed of moieties from all three reactants are formed.
The foregoing and other dyligomers can be mixed with a cross linker such as styrene, diallyl phthalate, triallyl cyanurate, a free radical catalyst and a catalyst such as cobalt naphthenate for the condensation of an isocyanate with a reactive hydrogen of an OH group to produce an intermediate that is stable for extended periods of time, and can be mixed with a diisocyanate or a polyisocyanate to produce a polymerizable composition in which the dyligomers and the diisocyanate or polyisocyanate undergo condensation polymerization to form urethane linkages and a three dimensional cross linked polymer and, subsequently and independently, the dyligomer reacts with the cross linker in an addition propagation reaction. The intermediate composition can also contain various fillers, a colorant, and water, if a cellular product is desired.